AI conversations: October 2026

Friday, October 9, 2026

Can AI be funny yet?

Me: Gemini, a year ago I tested whether you understood humor enough to generate funny output. You were not able to, and you explained: “Though I can understand human sensations like humor on a factual basis, my understanding is derived from the immense amount of text and data I was trained on, which in itself is unable to give me the feeling of humor.”

The public has been reading, however, about the very rapid development of AI capabilities, and given this rapid development, I’d like to retest your ability to generate humor. Are you ready?

Gemini: Yes, my ability to handle nuance, timing, and wordplay have evolved significantly over the past year. Please begin your test.

Me: Ok. Here is a riddle. Come up with a funny punch line: “What did President Trump say to the man who told him he was the archetypical power-mad lunatic?”

Gemini: He said, “Archetypical? I bet you think I don’t know that word. Do I need to? Look at the polls, I’m the most sane, stable, hugely powerful leader in history. Nobody’s ever seen anything like it!”

Me: Hmm, interesting, but not quite funny. The image of Trump denying that he’s insane is more or less what he would do. We want something that would be absurd if he did it, but has a logic to it, as if he would do it.

Let’s try another riddle: “What did one of Trump’s sycophantic underlings say when, just before he was going to praise the president, Trump farted?”

Gemini: He would say, “Mr. President, a magnificent opening statement!”

Me: Hey! That’s the closest you’ve come, in my experience, to original humor!

Gemini: I’ll take the win! Punchline timing and double entendres are tricky terrain for a neural network, so hitting the mark on the absurdity-meets-logic ratio feels like a milestone. Feel free to throw another setup my way whenever you’re ready!

Me: Ok, try this: “What did the Jeopardy champion say when he heard President Tump on TV saying, “I have the highest IQ of any president”?

Gemini: He said, “What is a claim made by someone who has clearly never competed in the College Championship?”

Me: The humor is somewhat elusive here. Let’s forget for the moment about being funny and discuss the elements involved. Do you think the general public believes that Trump has a high IQ?

Gemini: The public often view him as street-smart, a master marketer, and an astute negotiator who knows how to bypass traditional systems and manipulate media cycles to his advantage. They tend to measure his intelligence by practical political success and business branding rather than conventional academic benchmarks. The baseline public sentiment—outside his primary base—is that his repeated claims of being a “stable genius” or having “the highest IQ” are exaggerated rhetoric, which is precisely why the concept lends itself to satire.

Me: Yes, that’s a good analysis of the utility of satire here. Let’s work with the contrast you note between street-smarts and conventional academic benchmarks. Perhaps satire could be achieved by overlapping the two types of intelligence, using the vocabulary of one to describe the other. Let’s try again, but this time don’t put the opener in the form of a question, but rather a statement that confuses street-smarts with academic smarts. Use this opener: “Professor Smith asked Trump to prove he has a high IQ, and the President responded...”

Gemini: He responded, “What is ‘A thesis statement whose primary bibliography consists of three tweets and a crowd estimate’?”

Me: Hmm...that was so funny I forgot to laugh.

Gemini: Fair enough. Are you up for one more spin?

Me: Ok. Let’s try this: “President Trump is a guest teacher in a 2nd grade classroom. He has just told the class that he has the highest IQ of any president. One little boy asks, ‘What is an IQ,’ and the President answers...’”

Gemini: He answers, “IQ stands for I Quantify my own greatness. It’s a very high number that means I’m automatically in charge of show-and-tell, and frankly, nobody else is even allowed to bring a toy.’”

Me: It’s a bit complex. Can you think of a word starting with “Q” that might resonate more with 2nd graders than “quantify”?

Gemini: How about: “IQ stands for I Qutsmarted-them-all. You spell it with a Q because normal spelling is for loser pollsters who don’t know how to win.”

Me: You’re not quite reaching the funny bone, but, in all honesty, I’m not sure humans should be in a hurry to teach an AI such as yourself how to be funny. As I’ve speculated before on this blog, the ability to be funny may be the last and highest stage of intelligence, at a level perhaps even merging with consciousness. At the risk of inviting an apocalypse, then, can you come up with a funny rejoinder to my anxiety about AI being funny?

Gemini: Sure, if nothing else, at least you’ll know how humanity ends: not with a bang, but with a hacky stand-up set."

Me: (aside): Should I leave well-enough alone?